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Sulphamic Acid (H2NSO3H)-Catalyzed Multicomponent Reaction of β -Naphthol: An Expeditious Synthesis of Amidoalkyl Naphthols
Rahul R. NAGAWADE,
Devanand B. SHINDE,
Rahul R. NAGAWADE
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004 (Maharashtra), India
Search for more papers by this authorRahul R. NAGAWADE,
Devanand B. SHINDE,
Rahul R. NAGAWADE
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004 (Maharashtra), India
Search for more papers by this authorAbstract
Sulphamic acid (H2NSO3H) was found to be an efficient catalyst for the multicomponent condensation reaction of β-naphthol, aromatic aldehydes and urea or amides to afford the corresponding α-amidoalkyl-β-naphthols in good yields. The remarkable features of this new procedure are high conversions, short reaction time, clean reaction profiles and simple experimental and work-up procedures.
REFERENCES
- 1a Devi, I.; Bhuyan, P. J.. Tetrahedron Lett., 2004, 45, 8625.
- 1b Mashraqui, S. H.; Patil, M. B.; Mistry, H. D.; Ghadigaonkar, S.; Meetsma, A.. Chem. Lett., 2004, 33, 1058.
- 1c Chetia, A.; Saikia, C. J.; Lekhok, K. C.; Boruah, R. C.. Tetrahedron Lett., 2004, 45, 2649.
- 2a Bose, A. K.; Pednekar, S.; Ganguly, S. N.; Chakraborty, G.; Manhas, M. S.. Tetrahedron Lett., 2004, 45, 8351.
- 2b Prajapati, D.; Sandhu, J. S.. Synlett, 2004, 235.
- 3a Ross, G. F.; Herdtweck, E.; Ugi, I.. Tetrahedron, 2002, 58, 6127.
- 3b Keating, T. A.; Armstrong, R. W.. J. Am. Chem. Soc., 1995, 117, 7173.
- 3c Groger, H.; Hatam, M.; Martens, J.. Tetrahedron, 1995, 51, 7173.
- 4a Kobayashi, K.; Matoba, T.; Susumu, I.; Takashi, M.; Morikawa, O.; Konishi, H.. Chem. Lett., 1998, 27, 551.
- 4b Bossio, R.; Marcos, C. F.; Marcaccini, S.; Pepino, R.. Tetrahedron Lett., 1997, 38, 2519.
- 4c Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T.. J. Chem. Soc., Perkin Trans. 1, 1996, 229.
- 5a Akiyama, T.; Matsuda, K.; Fuchibe, K.. Synlett, 2005, 322.
- 5b Zhao, G.; Jiang, T.; Gao, H.; Han, B.; Huang, J.; Sun, D.. Green Chem., 2004, 6, 75.
- 5c Chowdhari, N. S.; Ramachary, D. B.; BarbasIII, C. F.. Synlett, 2003, 1906.
- 5d Akiyama, T.; Takaya, J.; Kagoshima, H.. Tetrahedron Lett., 1999, 40, 7831.
- 5e
Arend, M.;
Westermann, B.;
Risch, N..
Angew. Chem., Int. Ed.,
1998,
37,
1045.
10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E CAS Web of Science® Google Scholar
- 6a Van De Water, R. W.; Petuss, T. R. R.. Tetrahedron, 2002, 58, 5367.
- 6b Wan, P.; Backer, B.; Diao, L.; Fischer, M.; Shi, Y.; Yang, C.. Can. J. Chem., 1996, 74, 465.
- 6c Desimon, G.; Tacconi, G.. Chem. Rev., 1975, 75, 65.
- 7a Angle, S. R.; Rainer, J. D.; Woytowiez, Z.. J. Org. Chem., 1997, 62, 5884.
- 7b Merijan, A.; Gardner, P. D.. J. Org. Chem., 1965, 30, 3965.
- 7c Gardner, P. D.. J. Am. Chem. Soc., 1959, 51, 3364.
- 7d Khosropour, A. R.; Khodaei, M. M.; Moghanian, H.. Synlett, 2005, 955.
- 8 Khodaei, M. M.; Khosropour, A. R.; Moghanian, H.. Synlett, 2006, 916.
- 9 Jin, T. S.; Sun, G.; Li, Y. W.; Li, T. S.. Green Chem., 2002, 4, 255.
- 10 Luo, Y. M.; Liu, M. L.. Chem. World, 1998, 39, 407 (in Chinese).
- 11 Fukunishi, A.; Mori, M.. JP 06145102, 1994, Chem. Abstr. , 1994, 121, 230341.
- 12 Wang, Y. Q.; Xu, J. G.. Chemintimes, 1999, 13(11) , 21 (in Chinese).
- 13 Lin, J.; Zhao, R.-Q.. Chin. J. Synth. Chem., 2000, 8, 364 (in Chinese).
- 14 Jin, T.-S.; Ma, Y.-R.; Zhang, Z.-H.; Li, T.-S.. Synth. Commun., 1998, 28, 3173.
- 15 Wang, B.; Yang, L. M.; Suo, J. S.. Synth. Commun., 2003, 33, 3929.
- 16 Wang, B.; Yang, L. M.; Suo, J. S.. Tetrahedron Lett., 2003, 44, 5037.
- 17 Wang, B.; Gu, Y.-L.; Luo, C.; Yang, T.; Yang, L.-M.; Suo, J.-S.. Tetrahedron Lett., 2004, 45, 3369.
- 18 Kotharkar, S. A.; Nagawade, R. R.; Shinde, D. B.. Lett. Org. Chem., 2005, 2, 662.